1. Field of the Invention
The present invention relates to compositions of matter classified in the art of chemistry as .alpha.-[(lower alkylamino)alkyl]-4-hydroxy-3-(alkylthio, alkylsulfinyl or alkylsulfonyl)benzenemethanols, to processes and intermediates for the preparation thereof, and to a method of using the same for controlling tachycardia in mammals.
2. Prior Art
Continental Pharma British Specification No. 1,321,701, published June 27, 1973, discloses a group of compounds embraced by the generic formula: ##STR1## wherein, inter alia: R.sub.1 is RS, RSO or RSO.sub.2 (R.dbd.H, or C.sub.1 -C.sub.10 alkyl);
R.sub.2 and R.sub.3 are hydrogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; PA1 R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; and PA1 R.sub.5 and R.sub.6 are independently hydrogen or C.sub.1 -C.sub.16 alkyl. PA1 R.sub.1 represents a branched chain lower alkyl group of from 3 to 5 carbon atoms; and PA1 R.sub.2 represents hydrogen, methyl or ethyl. PA1 R.sub.2 is lower alkyl; PA1 Q is lower alkylthio, lower alkylsulfinyl or lower alkylsulfonyl; PA1 Y is hydrogen, lower alkanoyl, benzoyl or benzoyl substituted with from 1 to 2 methyl groups; and acid-addition salts thereof.
The compounds are stated to exhibit .beta.-adrenergic blocking, peripheral vasodilator, anti-arrhythmic and hypotensive activities.
Kaiser and Ross U.S. Pat. No. 3,917,704 issued Nov. 4, 1975, discloses a group of .alpha.-aminoalkyl-4-hydroxy-3-alkylsulfonylmethylbenzyl alcohols having the formula: ##STR2## wherein, inter alia: R represents lower alkyl of from 1 to 5 carbon atoms, straight or branched chain;
The compounds are stated to have utility as .beta.-adrenergic stimulants with relatively greater activity on respiratory smooth muscle than on cardiac muscle.
Kaiser, et al., J. Med. Chem. 18, 674-683 (1975) report essentially the work described in above-identified Kaiser and Ross U.S. Pat. No. 3,917,704 and in addition disclose the compound having the formula: ##STR3## which is stated to be weakly active as a .beta.-adrenergic agonist and which exhibits .beta.-adrenergic antagonistic activity. The work described in the Kaiser publication was reported orally Apr. 10, 1975 at the 169th national meeting of the American Chemical Society. An abstract of the oral presentation appeared at Abstracts of Papers, ACS Meeting 169: Medi 54 (April, 1975). l :
Lutz et al., J. Med. Chem. 15, 795-802 (1972), disclose the attempted preparation of 4-hydroxy-3-mercaptophenylethanolamine, i.e.: ##STR4## The compound however was neither isolated as a single entity nor characterized.
Pratesi, et al., British Specification 1,154,193 published June 4, 1969 discloses as a .beta.-adrenergic agent .alpha.-[(isopropylamino)methyl]-3-(methylthio)benzenemethanol, i.e.: ##STR5##